Brussels, Belgium to Chicago is an approximately 11.5-hour flight. You can also do a combination of train and flight. You'll gain 7 hours traveling from Brussels to Chicago due to the time zone difference. While traveling from Brussels, expect somewhat warmer days and about the same nights in Chicago, ranging from highs of 21°C to lows of 11°C. Finish your sightseeing early on the 19th (Sat) to allow enough time to travel to New York City.

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Plan for somewhat warmer nights when traveling from Chicago in October since evenings lows in New York City dip to 16°C. Finish up your sightseeing early on the 25th (Fri) so you can travel back home.